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If you’re dating an older woman, then there will be lots of excitement, adventures, and fun experiences ahead. If you’re nervous about how to go about it, just remember that the most important thing you can do is to have confidence in who you are and to not make such a big deal out of your age difference. Then just sit back, relax, and enjoy the relationship, just as you would do when dating a woman of any age.

Steps

Part 1

Making Her Want You

1

Exude confidence. If you really want to date an older woman, then you have to be secure in who you are. If you have low self-esteem or feel like you can’t hold your own in a romantic relationship, then you will have a hard time dating an older woman. Older women who date younger men aren’t looking to have a new son or someone to babysit; they want a man who knows who he is, no matter his age. If you lack confidence, then it’s time to work on loving yourself for who you are while also addressing your flaws.[1]

Avoid being too self-deprecating or saying negative things about yourself routinely. Focus on the things you do love about yourself.

Accept new challenges with excitement, instead of excuses for why you would fail at them.

Of course, it can take a long time to truly develop confidence, but you can take baby steps to address the flaws you can address and accept the ones you can’t. Make a list of all of the things you do like about yourself and work on expanding that list as you move forward.

Another part of being confident lies in being friends with people who make you feel good about yourself; if your friends are always putting you down, then you’re less likely to feel good about yourself.

2

Impress her with your independence. Older women don’t want little lapdogs who will follow them around everywhere they go; they want men who have their own friends, their own interests, and their own goals to pursue. Make sure that there’s a lot going on in your life other than the older woman, so that you can make time for her without wanting to see her 24/7. If the older woman feels like you have nothing going on except her, she’s likely to back away.

Plus, having your own interests, goals, and outside passions is a sign of maturity and character growth. If you don’t have much going on besides your video games, then the older woman is less likely to think that you’re a mature, dynamic person.

Continue spending time with your friends when you can. You shouldn’t drop everything to hang out with the older woman every time. Let her see that your friendships are important to you.

Don’t get jealous, either. If you often ask her where she’s been or how she’s been spending her time, she’ll feel like you’re not mature enough to trust her.

3

Take control when you can. Though you shouldn’t try to dominate the older woman, you don’t want to be completely passive and just to go along with anything she says just because you’re younger. Though she may have ideas about how you should spend your time together, make sure that you do some of the planning, too; you don’t want her to feel like it’s too much work to be with you. You should have ideas about where to dine, what movies to see, or what activities to do together, too.

Take turns deciding what to do on your dates. Just because she’s the older woman doesn’t mean she has to make all of the calls.

If you’re kissing or getting intimate, you can make the first move if you want to. You don’t want her to think you’re too timid.

Though taking control sometimes can show that you’re wise beyond your years, you should be okay with asking the older woman’s opinion when you genuinely don’t know what to do. Being able to admit when you don’t know something is actually a sign of maturity.

4

Use your age to your advantage. Don’t look at your age as something that’s holding you back and keeping you from enjoying your relationship with an older woman. After all, there must be a reason why she likes dating a younger guy, right? What you may lack in experience or knowledge, you gain in enthusiasm, excitement, energy, and a positive outlook. Show the older woman that there are benefits to dating a younger man, too.[3]

Impress her with your energy and your ability to try new things. Don’t be skeptical about trying something you’ve never even heard of before; instead, embrace new opportunities as they come.

Even if you haven’t done a lot, yet, you can talk about all of the things that you’re excited to try.

Don’t say, “I’m only eighteen, but…” You don’t want your age to look like a disadvantage.

5

Don’t make a big deal about her age. One thing you want to avoid if you want to have a successful relationship with an older woman is making a big deal about the fact that she is “the older woman.” Though some women are happy to talk about this, other women don’t want to be looked at as “older” and just want to enjoy their relationships on their own terms.[4]

You don’t want to accidentally insult the woman you’re dating; unless she brings it up, try not to draw too much attention to her age.

Making a big deal about her age will make her feel like you’re not comfortable with dating someone with so much more experience than you. This will make you come off as a bit insecure.

6

Don’t change too much for her. You may feel like you need a complete personality makeover to have a successful relationship with an older woman. However, if you change too much, then the woman will lose sight of the man she was attracted to, at first. Though you may work on gaining experience, becoming more mature, and holding your own in the relationship, you shouldn’t change yourself so completely that the older woman doesn’t even recognize the guy who asked her out.

At the end of the day, you want the older woman to like you for you, not for some polished, dressed up version of who you are. If you feel like you’re not being true to yourself anymore, then you need to stop.

If you really want to have a meaningful relationship with an older woman, then you shouldn’t hide important parts of yourself just to seem older. Let her know who you really are.

Part 2

Being an Amazing Boyfriend

1

Be a gentleman. If you want to successfully date an older woman, then you have to be a true gentleman. You don’t want her to think that you don’t have manners or that you don’t know how to treat a woman. Now, some women think that certain “gentlemanly” traits, such as holding doors or pushing out chairs, are antiquated, so try to get a read on her expectations. Still, it doesn’t hurt to be polite, to have good manners, and to avoid overly vulgar topics. If you want to be a true gentleman, the most important thing is that you’re respectful of your date.[5]

Show up to your dates on time and sometimes even with a small gift.

Make sure to put an effort into your appearance before you go on a date. You want the older woman to see that she’s worth it.

Give her compliments to show how beautiful and amazing you think she is.

Treat everyone around you with respect as well. Being kind and polite to servers, friends, and strangers shows that you’re a respectful person and that you’re not just putting on an act for the woman.

2

Don’t worry about your lack of experience. Sure, the older woman has probably had more life experience and has been with more people than you have. That doesn’t mean you have to talk about it all the time or worry that you don’t have enough to bring to the table. If she’s more experienced in the bedroom, then great—enjoy whatever it is that she’s going to teach you. Try not to focus on your past and think about enjoying the experience you’re gaining with the older woman in the present.[6]

If you want to be a good boyfriend, then you really don’t have to bring up your lack of experience. For one thing, it may make the older woman feel self-conscious about the amount of experience she has. For another, it’ll make you look insecure.

When you’re getting intimate, try not to worry about it if you don’t have very much experience in that department. If you obsess over this, then it’ll keep you from enjoying yourself.[7]

3

Be assertive. Be a man who knows what he wants and isn’t afraid to ask for it. If you’re always second-guessing yourself, mumbling, or waiting to say what’s really on your mind, then your older woman may start looking for someone more assertive. Get comfortable telling her what you’d like to do on your dates, letting her know if she hurt your feelings, and asking for what you want.[8]

Part of being assertive means having a firm, clear voice when the time comes to say something. If you talk too quietly or stumble over your words a lot, then you’ll have trouble being assertive.[9]

While you shouldn’t interrupt the older woman when she’s talking, you should be comfortable with articulating what’s on your mind when it’s your time to talk.

4

Be mature. Though you may not be the most mature guy in the world, you can certainly make an effort to become more worldly. Avoid having temper tantrums, getting angry over stupid little things, or just generally looking like you have no idea what’s going on. Make an effort not to look clueless and to read up on something if you don’t have any idea how it works. Learn to be polite to others and to treat them with respect instead of just looking out for yourself. Your older woman will want a man who is mature enough for her.[10]

Avoid whining or complaining about insignificant matters too much. This is a sign of a true lack of maturity.

Avoid childish habits such as biting your nails, making fun of people, or fighting with your siblings.

Try not to get overly angry or upset when things don’t go your way.

5

Keep things fun and light. The older woman you’re dating may have had her fair share of serious older men. You can show her that you’re different by keeping things upbeat, fun, and lighthearted, so that she enjoys your time together. Minimize the serious talks and conversations about “Where is this going?” if you know what’s good for you. Work on enjoying your relationship in the moment instead of worrying about what lies ahead.

Stick to fun, lighthearted topics and make her laugh. Show her how much fun you can be.

Of course, you can open up to her and share more serious things about yourself when you’re ready. But as a rule, you should keep things fun and easy.

6

Don’t bring up your age difference all the time. If you want the relationship to last, then you can’t go around talking about how much older than you she is all the time. You want her to see that you want her for her, instead of because you think it’s hot and exciting to date a woman who is older than you. If you keep bringing it up, then she’ll get the sense that your heart isn’t in the right place.[11]

Fine, if she brings it up and wants to laugh about it, then you should join in. But if she doesn’t mention it, then neither should you.

Part 3

Making It Last

1

Show a real interest in who she is. If you really want to have a successful and long-lasting relationship with an older woman, then you have to do more than just think of her as that sexy older woman you’ve been seeing. You have to make an effort to get to know the person who she really is and to remember that age is just a number. Let her see that you care about getting to know her and that you truly value the time you spend together.[12] Here’s how:

Take the time to really listen to her when she talks to you. Put away your phone, make eye contact, and don’t interrupt her.

Ask her questions about her childhood, her work, her friends, her family, and the things that interest her. Show her that you really want to know everything about her.

Check in with her when you’re apart to show that you care about how her day is going and that you’re thinking of her.

Give her compliments that show her that she really stands out to you. Don’t just tell her she’s hot; compliment her sense of humor or other aspects of her personality that really matter.

2

Give her space. If you want to make your relationship last, then you can’t be clingy. You have to respect the fact that your older woman is her own person and that she has a life going on outside of being with you. This could mean her time at work, spending nights with her girlfriends, or all of the time she spends doing her own thing, whether it’s yoga, writing poetry, or cooking. Don’t be needy or ask her to hang out with you all the time, and appreciate the fact that she has a life outside of your relationship.[13]

Show an interest in the things she does when you’re not together. Ask her about her friends, her job, and her hobbies to show that you care.

You can check in with her when you’re apart, but don’t call her three times when she’s hanging out with her girlfriends; you don’t want her to think that you have nothing else going on or that you’re jealous.

3

Learn to hold up your end of the conversation. If you want to make your relationship last, then you should be able to hold your own when it comes to having a conversation with your girlfriend. You don’t want her to feel like she’s doing all of the talking or like you don’t have any opinions of your own to contribute. You have to show her that you’re thoughtful, mature, and articulate if you want to keep her interested.

Read up on politics, world news, and other timely events. If she brings up a current event, you don’t want to look completely clueless.

Talk about your experiences, such as your childhood memories or any traveling you’ve done. Don’t think that your experiences aren’t valid just because you’re younger.

If something funny happened to you that day, then get comfortable sharing it. Don’t think that it has to be all serious just because you’re with a mature woman.

Avoid talking about topics that make you sound young. If you got in a silly fight with your roommate or have to beg your parents for money, then these topics may be best avoided.

4

Keep things exciting. If you want your relationship to last, then you can’t keep doing the same old thing with your girlfriend every time you go out. Be on the lookout for new restaurants to try, new places to visit, and new activities to try together, from taking salsa lessons to cooking an Italian meal together.[14] If you get too comfortable doing the same thing together day after day, then you may come off as complacent and the older woman, who has more experience, may be wanting something more.

Though it’s great to develop some traditions to do together, you don’t want to fall into the same old dull routine day after day. Make sure you do something new together at least once a week.

Write her a love letter telling her how much she means to you just because. Don’t think that the romance has to stop just because you’ve been together for a while.

Be spontaneous. Suggest a weekend trip the day before, or take her on a surprise date to do something she’s always wanted to try, such as rock climbing.

5

See if it’s meant to last. After you’ve been with your older woman for a while, you can start to ask yourself if it’s meant to be. If you feel like you’ve forgotten all about your age difference and that you have a meaningful, fun, and fulfilling relationship, then hats off to you. However, if you find that the most exciting thing about your relationship is your age difference and that that has worn off, then it’s time to move on.

If you find that dating an older woman was just a novelty, then you may not be in the relationship for the right reasons.

Be honest with yourself. If the older woman wants more than you are comfortable giving her, then you may have to part ways.

However, if you’re having an amazing time dating an older woman, then continue to enjoy your amazing relationship for as long as you want.[15]

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To date an older woman, be a gentleman by showing up on time, putting an effort into your appearance, and giving her compliments. You should also voice your opinions and hold up your end of the conversation since older women like men who are thoughtful, articulate, and mature. Another way to hold her interest is to be independent, like having your own friends and hobbies. Don’t make a big deal about her age or else she might sense that you’re uncomfortable with it. Instead, focus on showing her how confident and capable you are by standing tall, making eye contact, and accepting new challenges with excitement. To learn how to make a relationship with an older woman last, keep reading!

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Article Info

This article was co-authored by our trained team of editors and researchers who validated it for accuracy and comprehensiveness. Together, they cited information from 15 references. wikiHow's Content Management Team carefully monitors the work from our editorial staff to ensure that each article meets our high standards.

Thanks to all authors for creating a page that has been read 277,338 times.

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Co-Authored By:

wikiHow Staff Editor

Co-authors: 11

Updated: July 9, 2019

Views: 277,338

91% of readers found this article helpful.

11 votes - 91%

Click a star to add your vote

91% of people told us that this article helped them.

SJ

Sean P. Jhala

Jun 26

"This article helped me a lot and changed my relationship. Now I can go for months without remembering our age difference. Even my friends love her and have made her part of our lives."..." more

ZM

Zack May

Feb 25, 2018

"I liked how in-depth this article is and how well written it is. I took all the advice given and applied to my love life. I can say without a doubt, a must-read for anyone who is looking to date an older woman."..." more

DW

David Wong

Apr 4, 2016

"I have yet to embark on a date with an older women. It scares me a little, after reading this how-to I feel much more prepared. I will make sure to not make a big deal about her age. "..." more

RT

Rique Tony

Feb 19, 2017

"The article is comprehensive and explores every trivial detail crucial to dating older women. Personally, I am thrilled!!"..." more

JM

Jhone Mu

Oct 28, 2017

"I'd love to have a girlfriend who is 20 years older than me, they're so attractive and pretty."

SG

Sepehr Goudarzi

Apr 16, 2017

"I did not try it yet, but I think it would work for my relationship. Thank you very much."